Visible-light-enabled ruthenium-catalyzed para-C−H difluoroalkylation of anilides
-
* Corresponding author.
E-mail address: chemagh@163.com (G. An).
Citation:
Yaohang Cheng, Xian Zhang, Guanghui An, Guangming Li, Zhenyu Yang. Visible-light-enabled ruthenium-catalyzed para-C−H difluoroalkylation of anilides[J]. Chinese Chemical Letters,
;2023, 34(3): 107625.
doi:
10.1016/j.cclet.2022.06.048
J.A. Leitch, C.G. Frost, Chem. Soc. Rev. 46 (2017) 7145–7153.
doi: 10.1039/C7CS00496F
M.C. Kozlowski, Acc. Chem. Res. 50 (2017) 638–643.
doi: 10.1021/acs.accounts.6b00637
Q. Shao, K. Wu, Z. Zhuang, S. Qian, J.Q. Yu, Acc. Chem. Res. 53 (2020) 833–851.
doi: 10.1021/acs.accounts.9b00621
C. Ding, Y. Ren, C. Sun, J. Long, G. Yin, J. Am. Chem. Soc. 143 (2021) 20027–20034.
doi: 10.1021/jacs.1c09214
B. Zhao, Y. Li, H. Li, et al., Sci. Bull. 66 (2021) 570–577.
doi: 10.1016/j.scib.2020.10.001
P. Gandeepan, L. Ackermann, Chem 4 (2018) 199–222.
doi: 10.1016/j.chempr.2017.11.002
J. Börgel, T. Ritter, Chem 6 (2020) 1877–1887.
doi: 10.1016/j.chempr.2020.07.007
L. Ackermann, K. Korvorapun, R.C. Samanta, T. Rogge, Synthesis 53 (2021) 2911–2946
doi: 10.1055/a-1485-5156
U. Dutta, S. Maiti, T. Bhattacharya, D. Maiti, Science 372 (2021) eabd5992.
doi: 10.1126/science.abd5992
L. Ackermann, Acc. Chem. Res. 47 (2014) 281–295.
doi: 10.1021/ar3002798
K. Korvorapun, N. Kaplaneris, T. Rogge, et al., ACS Catal. 8 (2018) 886–892.
doi: 10.1021/acscatal.7b03648
Z. Gan, X. Zhu, Q. Yan, X. Song, D. Yang, Chin. Chem. Lett. 32 (2021) 1705–1708.
doi: 10.1016/j.cclet.2020.12.046
Q. Yan, W. Cui, J. Li, et al., Org. Chem. Front. 9 (2022) 2653–2658.
doi: 10.1039/d1qo01910d
D. Yang, Q. Yan, E. Zhu, J. Lv, W.M. He, Chin. Chem. Lett. 33 (2022) 1798–1816.
doi: 10.1016/j.cclet.2021.09.068
X. Zhu, M. Jiang, X. Li, et al., Org. Chem. Front. 9 (2022) 347–355.
doi: 10.1039/d1qo01570b
G.B. Boursalian, W.S. Ham, A.R. Mazzotti, T. Ritter, Nat. Chem. 8 (2016) 810–815.
doi: 10.1038/nchem.2529
C.L. Ciana, R.J. Phipps, J.R. Brandt, F.M. Meyer, M.J. Gaunt, Angew. Chem. Int. Ed. 50 (2011) 458–462.
doi: 10.1002/anie.201004703
N.A. Romero, K.A. Margrey, N.E. Tay, D.A. Nicewicz, Science 349 (2015) 1326–1330.
doi: 10.1126/science.aac9895
S. Bag, T. Patra, A. Modak, et al., J. Am. Chem. Soc. 137 (2015) 11888–11891.
doi: 10.1021/jacs.5b06793
M.E. Hoque, R. Bisht, C. Haldar, B. Chattopadhyay, J. Am. Chem. Soc. 139 (2017) 7745–7748.
doi: 10.1021/jacs.7b04490
G. Meng, N.Y.S. Lam, E.L. Lucas, et al., J. Am. Chem. Soc. 142 (2020) 10571–10591.
doi: 10.1021/jacs.0c04074
T. Patra, S. Bag, R. Kancherla, et al., Angew. Chem. Int. Ed. 55 (2016) 7751–7755.
doi: 10.1002/anie.201601999
B.E. Haines, Y. Saito, Y. Segawa, K. Itami, D.G. Musaev, ACS Catal. 6 (2016) 7536–7546.
doi: 10.1021/acscatal.6b02317
H. Qiao, S. Sun, F. Yang, et al., Org. Lett. 17 (2015) 6086–6089.
doi: 10.1021/acs.orglett.5b03114
Y. Saito, Y. Segawa, K. Itami, J. Am. Chem. Soc. 137 (2015) 5193–5198.
doi: 10.1021/jacs.5b02052
C. Tian, X. Yao, W. Ji, et al., Eur. J. Org. Chem. 2018 (2018) 5972–5979.
doi: 10.1002/ejoc.201801058
X.G. Wang, Y. Li, L.L. Zhang, et al., Chem. Commun. 54 (2018) 9541–9544.
doi: 10.1039/C8CC05067H
C. Yuan, L. Zhu, C. Chen, et al., Nat. Commun. 9 (2018) 1189.
doi: 10.1038/s41467-018-03341-6
C. Yuan, L. Zhu, R. Zeng, Y. Lan, Y. Zhao, Angew. Chem., Int. Ed. 57 (2018) 1277–1281.
doi: 10.1002/anie.201711221
B. Berzina, I. Sokolovs, E. Suna, ACS Catal. 5 (2015) 7008–7014.
doi: 10.1021/acscatal.5b01992
J.A. Leitch, C.L. McMullin, A.J. Paterson, et al., Angew. Chem., Int. Ed. 56 (2017) 15131–15135.
doi: 10.1002/anie.201708961
J.M. Li, Y.H. Wang, Y. Yu, et al., ACS Catal. 7 (2017) 2661–2667.
doi: 10.1021/acscatal.6b03671
S. Liang, M. Bolte, G. Manolikakes, Chem. Eur. J. 23 (2017) 96–100.
doi: 10.1002/chem.201605101
J. Wang, Y.B. Pang, N. Tao, R. Zeng, Y. Zhao, Org. Lett. 22 (2020) 854–857.
doi: 10.1021/acs.orglett.9b04327
X. Wang, D. Leow, J.Q. Yu, J. Am. Chem. Soc. 133 (2011) 13864–13867.
doi: 10.1021/ja206572w
Y. Han, G. Li, L. Liu, et al., Org. Chem. Front. 7 (2020) 1823–1827.
doi: 10.1039/d0qo00402b
P. Liu, C. Chen, X. Cong, J. Tang, X. Zeng, Nat. Commun. 9 (2018) 4637.
doi: 10.1038/s41467-018-07069-1
P. Liu, N. Hao, D. Yang, et al., Org. Chem. Front. 8 (2021) 2442–2448.
doi: 10.1039/d1qo00243k
S. Okumura, Y. Nakao, Org. Lett. 19 (2017) 584–587.
doi: 10.1021/acs.orglett.6b03741
S. Okumura, S. Tang, T. Saito, et al., J. Am. Chem. Soc. 138 (2016) 14699–14704.
doi: 10.1021/jacs.6b08767
L. Yang, K. Semba, Y. Nakao, Angew. Chem., Int. Ed. 56 (2017) 4853–4857.
doi: 10.1002/anie.201701238
C. Yuan, P. Dai, X. Bao, Y. Zhao, Org. Lett. 21 (2019) 6481–6484.
doi: 10.1021/acs.orglett.9b02362
S. Okumura, T. Komine, E. Shigeki, K. Semba, Y. Nakao, Angew. Chem., Int. Ed. 57 (2018) 929–932.
doi: 10.1002/anie.201710520
M.O. Anderson, J. Zhang, Y. Liu, et al., J. Med. Chem. 55 (2012) 5942–5950.
doi: 10.1021/jm300491y
J.O. Link, J.G. Taylor, L. Xu, et al., J. Med. Chem. 57 (2014) 2033–2046.
doi: 10.1021/jm401499g
N.A. Meanwell, J. Med. Chem. 54 (2011) 2529–2591.
doi: 10.1021/jm1013693
S. Purser, P.R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 37 (2008) 320–330.
doi: 10.1039/B610213C
Z.X. Ruan, S.K. Zhang, C.J. Zhu, et al., Angew. Chem. Int. Ed. 56 (2017) 2045–2049.
doi: 10.1002/anie.201611595
Z. Feng, Y.L. Xiao, X. Zhang, Acc. Chem. Res. 51 (2018) 2264–2278.
doi: 10.1021/acs.accounts.8b00230
Y. Cheng, Y. He, J. Zheng, et al., Chin. Chem. Lett. 32 (2021) 1437–1441.
doi: 10.1016/j.cclet.2020.09.044
W.T. Fan, Y. Li, D. Wang, S.J. Ji, Y. Zhao, J. Am. Chem. Soc. 142 (2020) 20524–20530.
doi: 10.1021/jacs.0c09545
X. Fang, Y. Tan, L. Gu, L. Ackermann, W. Ma, ChemCatChem 13 (2021) 1738–1742.
doi: 10.1002/cctc.202002056
Y.J. Mao, B.X. Wang, Q.Z. Wu, et al., Chem. Commun. 55 (2019) 2019–2022.
doi: 10.1039/c8cc09129c
G. Tu, D. Wang, C. Yuan, J. Zhang, Y. Zhao, J. Org. Chem. 85 (2020) 10740–10749.
doi: 10.1021/acs.joc.0c01257
G. Tu, C. Yuan, Y. Li, J. Zhang, Y. Zhao, Angew. Chem., Int. Ed. 57 (2018) 15597–15601.
doi: 10.1002/anie.201809788
W.K. Tang, F. Tang, J. Xu, et al., Chem. Commun. 56 (2020) 1497–1500.
doi: 10.1039/c9cc09586a
J. Zhou, F. Wang, Z. Lin, et al., Org. Lett. 22 (2020) 68–72.
doi: 10.1021/acs.orglett.9b03923
P. Gandeepan, J. Koeller, K. Korvorapun, J. Mohr, L. Ackermann, Angew. Chem. Int. Ed. 58 (2019) 9820–9825.
doi: 10.1002/anie.201902258
A. Sagadevan, M.F. Greaney, Angew. Chem. Int. Ed. 58 (2019) 9826–9830.
doi: 10.1002/anie.201904288
J. Gao, Y.H. Guo, Y.P. Wang, X.J. Wang, W.S. Xiang, Chin. Chem. Lett. 22 (2011) 1159–1162.
Q. Yu, L. a. Hu, Y. Wang, S. Zheng, J. Huang, Angew. Chem. Int. Ed. 54 (2015) 15284–15288.
doi: 10.1002/anie.201507100
G. Marinescu, D.C. Culita, C. Romanitan, et al., Appl. Surf. Sci. 520 (2020) 146379.
doi: 10.1016/j.apsusc.2020.146379
B.A. Lakshmi, J.Y. Bae, J.H. An, S. Kim, Inorg. Chim. Acta 495 (2019) 118989.
doi: 10.1016/j.ica.2019.118989
Z. Qu, K. Wu, W. Meng, et al., Chem. Eng. J. 397 (2020) 125416.
doi: 10.1016/j.cej.2020.125416
K. Korvorapun, J. Struwe, R. Kuniyil, et al., Angew. Chem. Int. Ed. 59 (2020) 18103–18109.
doi: 10.1002/anie.202003035
A. Sagadevan, A. Charitou, F. Wang, et al., Chem. Sci. 11 (2020) 4439–4443.
doi: 10.1039/d0sc01289k
Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
Huarui Han , Yangrui Xu , Yu Cheng , Liguang Tang , Jie Jin , Xinlin Liu , Changchang Ma , Ziyang Lu . Frustrated Lewis pairs in CO2 photoreduction: A review on synergistic activation and charge separation. Chinese Journal of Structural Chemistry, 2025, 44(10): 100728-100728. doi: 10.1016/j.cjsc.2025.100728
Yanghanbin Zhang , Dongxiao Wen , Wei Sun , Jiahe Peng , Dezhong Yu , Xin Li , Yang Qu , Jizhou Jiang . State-of-the-art evolution of g-C3N4-based photocatalytic applications: A critical review. Chinese Journal of Structural Chemistry, 2024, 43(12): 100469-100469. doi: 10.1016/j.cjsc.2024.100469
Guixu Pan , Zhiling Xia , Ning Wang , Hejia Sun , Zhaoqi Guo , Yunfeng Li , Xin Li . Preparation of high-efficient donor-π-acceptor system with crystalline g-C3N4 as charge transfer module for enhanced photocatalytic hydrogen evolution. Chinese Journal of Structural Chemistry, 2024, 43(12): 100463-100463. doi: 10.1016/j.cjsc.2024.100463
Zhou Li , Mengxue Yu , Shixin Chang , Zhibin Huang , Zhenmin Cheng , Weibin Zhang , Sónia A. C. Carabineiro , Zhigao Xu , Kangle Lv . Enhancing the photocatalytic activity of crystalline g-C3N4 towards NO oxidation and CO2 reduction through K+-doping and cyano defect engineering. Chinese Journal of Structural Chemistry, 2026, 45(1): 100698-100698. doi: 10.1016/j.cjsc.2025.100698
Zhen Shi , Wei Jin , Yuhang Sun , Xu Li , Liang Mao , Xiaoyan Cai , Zaizhu Lou . Interface charge separation in Cu2CoSnS4/ZnIn2S4 heterojunction for boosting photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100201-100201. doi: 10.1016/j.cjsc.2023.100201
Qiang Zhang , Weiran Gong , Huinan Che , Bin Liu , Yanhui Ao . S doping induces to promoted spatial separation of charge carriers on carbon nitride for efficiently photocatalytic degradation of atrazine. Chinese Journal of Structural Chemistry, 2023, 42(12): 100205-100205. doi: 10.1016/j.cjsc.2023.100205
Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
Tianhao Li , Wenguang Tu , Zhigang Zou . In situ photocatalytically enhanced thermogalvanic cells for electricity and hydrogen production. Chinese Journal of Structural Chemistry, 2024, 43(1): 100195-100195. doi: 10.1016/j.cjsc.2023.100195
Shuhong Wu , Wanying Han , Ying Wang , Yan Zhuang , Hui Niu , Lurong Li , Junhui Wang , Yuan Liu , Huan Lin , Kaifeng Wu , Jinni Shen , Yingguang Zhang , Michael K. H. Leung , Jinlin Long . Close π-π stacking facilitated intermolecular charge separation in self-assembled perylene monoimide for photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(6): 100592-100592. doi: 10.1016/j.cjsc.2025.100592
Cui Luo , Peng-Hui Li , Wei-Ming Liao , Qia-Chun Lin , Xiao-Xiang Zhou , Jun He . Strategic metal substitution for enhanced visible-light-driven oxygen evolution in heterometallic MOFs. Chinese Journal of Structural Chemistry, 2025, 44(7): 100621-100621. doi: 10.1016/j.cjsc.2025.100621
Chao Wei , Zi-Yi Zhao , Jing-Jing Li , Jinli Zhang , Ming Lu , Xiao-Qin Liu , Guoliang Liu , Jiandong Pang , Lin-Bing Sun . Topology guided construction of MOF by linking Zr-MOLs with perylene diimide motifs for photocatalytic oxidation. Chinese Journal of Structural Chemistry, 2025, 44(8): 100625-100625. doi: 10.1016/j.cjsc.2025.100625
Na Lu , Tingting Pang , Xuedong Jing , Yongan Zhu , Linqun Yu , Sining Ben , Yuchan Song , Shiwen Du , Wei Lu , Zhenyi Zhang . Optimizing the Schottky Barrier in AuAg Alloy Decorated TiO2 Nanofibers to Enhance Hot-Electron-Induced CO2 Reduction. Chinese Journal of Structural Chemistry, 2025, 44(8): 100633-100633. doi: 10.1016/j.cjsc.2025.100633
Anna Dai , Zhenxiong Huang , Li Tian , Zheng Zhang , Xiangjiu Guan , Liejin Guo . Polymeric Carbon Nitride for Photocatalytic Overall Water Splitting: Modification Strategies and Recent Advances. Chinese Journal of Structural Chemistry, 2025, 44(8): 100630-100630. doi: 10.1016/j.cjsc.2025.100630
Wanxin Hu , Yan Shi , Junxia Yu , Haiyang Shi , Yingping Huang , Ruiping Li . Engineering 2D/2D FeOOH/BiOCl S-scheme heterojunction toward efficient and stable tetracycline photodegradation. Chinese Journal of Structural Chemistry, 2026, 45(3): 100832-100832. doi: 10.1016/j.cjsc.2025.100832
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250